36 of Princess Diana's most daring outfits

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diana fashion
Princess Diana is a fashion icon.Anwar Hussein/Getty/Anwar Hussein/WireImage/Getty/Tim Graham Photo Library via Getty Images
  • Princess Diana is known for many things, including her colorful and daring style.

  • Some famous looks are the off-the-shoulder "Revenge Dress" and casual Virgin-Atlantic sweatshirt.

  • The princess is known for wearing beautiful gowns, including her wedding dress with a 25-foot train.

While she was engaged to Prince Charles, Princess Diana looked elegant in this blue, winter look.

princess diana winter fashion
Diana, Princess of Wales, arriving at a Christmas service wearing a hat and muff.Tim Graham Photo Library/Getty Images

For Christmas 1981, the soon-to-be princess entered the church in a long blue coat and tall black boots. She finished off the wintery look with a matching hat and muff.

Princess Diana's wedding gown had a magnificently long train.

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The train on Princess Diana's wedding dress was 25 feet long.Fox Photos / Stringer

For her 1981 wedding to Prince Charles, Diana wore a gown that fully embraced the style of the 1980s with its giant, puffy sleeves.

That said, the most iconic and daring part of this gown is its train. The train was 25 feet long, the longest in royal-wedding history.

Her honeymoon dress was light and colorful.

princess diana honeymoon
Princess Diana wore this dress while leaving the airport.Kypros / Contributor

In 1981, Princess Diana left for her honeymoon in this light, flowery wrap dress by Donald Campbell. She paired it with a pearl choker.

The princess stunned in this red, shoulder-baring gown in the summer of 1981.

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Princess Diana wearing a Bellville Sassoon evening gown.Bob Thomas/Popperfoto via Getty Images/Getty Images

Princess Diana wore a stunning red, sparkly gown by Bellville Sassoon to an event in 1981. She donned red and silver jewelry and carried a silver clutch to complement the ensemble.

Princess Diana wasn't afraid to show off her casual style in pastel-yellow overalls.

princess diana overalls 1981
Diana, Princess of Wales, at a polo match in summer 1981.Tim Graham Photo Library via Getty Images

The princess wore plenty of elegant gowns, but her casual fashion moments were just as enviable.

She wore these yellow overalls over a colorful floral top to a polo match in July 1981. The look was finished off with red espadrille wedges and big sunglasses.

Princess Diana wore this dreamy gown the day before it was announced that she was pregnant with Prince William.

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Once again, Princess Diana paired the dress with a pearl choker.Tim Graham / Contributor/Getty

This gauzy, off-the-shoulder dress, with swirls of lilac and pink, has a dreamy quality to it.

She wore this look in 1981 on the day before the palace announced that she was pregnant with Prince William.

Princess Diana's maternity looks were just as stylish and daring as her everyday ones.

princess diana maternity
A pregnant Princess Diana in a red David Sassoon maternity gown in 1982.Anwar Hussein/Getty Images

The princess wore this bold, Shakespearean-esque gown by David Sassoon to attend a function at the Barbican Centre in 1982 while she was pregnant with Prince William.

Princess Diana rocked some bold colors and fabrics while she was pregnant with Prince William.

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Princess Diana wore this fuzzy woolen coat in 1982.Hulton Archive/Getty

Princess Diana donned some stunning maternity outfits, including this red woolen coat and hat over a frilly blue blouse during a 1982 visit to the Grand National in Aintree.

Shortly after Prince William's birth, she looked elegant in polka dots.

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Princess Diana and Prince Charles with their newborn son Prince William in 1982.Princess Diana Archive / Stringer / Getty

Princess Diana's patterned teal dress was colorful and fun.

Kate Middleton seemingly channeled Princess Diana's 1982 polka-dotted look for her own post-pregnancy photos in 2013.

Shortly after giving birth to Prince George, Middleton wore a light-blue polka-dot frock.

Princess Diana paired elegant jewels with vibrant colors.

princess diana pink
Princess Diana wore this dress with the Spencer-family tiara in 1983.Anwar Hussein/Getty

In 1983, Princess Diana bared her shoulders in this bright-pink, spaghetti-strap gown.

The princess paired the dress with the famed Spencer-family tiara.

She could sometimes be spotted in a bow tie, too.

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Princess Diana wore this outfit while attending a concert.David Levenson / Contributor

Princess Diana may have been known for her elaborate dresses, but she has also worn some memorable suits.

Here she is in 1984 attending a rock concert while wearing a black-and-white tuxedo-style suit.

She danced with John Travolta in an elegant velvet gown.

princess diana john travolta
John Travolta and Princess Diana dancing in 1985.Anwar Hussein / Contributor/Getty

In 1985, Princess Diana wore this dark velvet gown and paired it with her famed pearl choker.

Here, she's dancing with actor John Travolta at the White House in Washington DC.

She's worn some sparkling, open-back numbers, too.

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Princess Diana wore this Bruce Oldfield dress to a movie premiere.Tom Wargacki/WireImage

Princess Diana was glittering in silver at the 1985 premiere of the James Bond movie "A View to a Kill."

The gown was complete with an open back, a style that's quite uncommon for a member of the royal family to wear.

Princess Diana has also worn some polished, striped looks.

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Princess Diana wore this Catherine Walker ensemble during a tour of Italy.David Levenson/Getty Images

While visiting a naval base during a 1985 royal tour of Italy, Princess Diana wore a pinstriped dress by Catherine Walker and paired it with a simple hat.

Princess Diana truly embraced the style of the 1980s in this shoulder-padded frock.

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Princess Diana also wore this purple dress while she was in Italy.Princess Diana Archive / Stringer/Getty

In another iconic look from 1985, Princess Diana chose this star-patterned, drop-waist gown for another event in Italy.

The dress even featured shoulder pads, a 1980s signature.

The princess also wore some color-blocked looks.

princess diana 1985
Color blocking was a popular trend in the 1980s.Tim Graham / Contributor/Getty

Princess Diana also embraced color blocking, another popular trend throughout the 1980s.

She wore this bold blue and black Bruce Oldfield dress in 1985 on her trip to Venice, Italy.

Princess Diana knew how to style a casual look.

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This time, the princess channeled a trend from the 1950s.Tim Graham / Contributor/Getty

Pedal pushers may have been popular in the 1950s, but the princess brought them back in 1986 during a day off at home.

The gingham-patterned pants and vibrant-pink sweater took the casual look to new heights.

The princess wore another bold, androgynous look while visiting Portugal.

princess diana portugal 1987 bow tie
Princess Diana during an official visit to Portugal in 1987.07919595Globe Photos/MediaPunch /IPX LISBON/AP

During an official visit to Portugal in February 1987, the princess rocked another bow-tie look. She paired the statement accessory with an orange satin jacket and a long black skirt.

She rocked another casual overall look to a polo match in 1987.

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Diana, The Princess Of Wales, and Prince William at a polo match in June 1987.Julian Parker/UK Press/Getty Images

By 1987, Princess Diana had mastered the casual summer look.

She wore these overalls with a rope-belt detail to a polo match with her son, Prince William.

The royal looked great in a yellow, summery look on vacation in Spain.

princess diana
Princess Diana with Prince William and Prince Harry in Spain.ASSOCIATED PRESS

During a 1987 trip to Majorca, Princess Diana was dressed for the summer weather in this yellow linen two-piece set. She finished off the bright look with gold flats and jewelry.

Her sons' vibrantly colored outfits also complemented her yellow outfit.

The princess was always on trend while she was on the slopes.

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Princess Diana during a skiing holiday in Klosters, Switzerland, in March 1988.James Andanson/Sygma/Getty Images

Princess Diana wore this black, green, and pink snowsuit for a few different skiing trips, including her vacation to Switzerland in 1988.

She finished off the sporty look with a white turtleneck and mirrored sunglasses.

In 1988, the princess showed her accessorizing prowess.

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Princess Diana wore this look to Bangkok, Thailand.Georges De Keerle / Contributor/Getty

During an official 1988 visit to Bangkok, Thailand, Princess Diana looked chic in this cinched dress paired with white sunglasses and a vibrant teal belt.

The princess wore many bold hats, including this elegant birdcage one.

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Diana, the Princess of Wales, during a visit to Paris in 1988.Reuters

Princess Diana wore this statement hat by Viv Knowland during a 1988 trip to Paris to attend an armistice commemoration.

Princess Diana loved her pearls — and sometimes she wore them head-to-toe.

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This white pearl dress is currently in the Victoria and Albert Museum.Tim Graham Photo Library via Getty Images

Some people have compared this 1989 look to something the musician Elvis would wear.

The pearl-covered gown is currently at the Victoria and Albert Museum in London.

The princess could also pull off a casual, mismatched look.

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Princess Diana wore an oversized blazer with a sweatshirt, sweatpants, and cowboy boots.Tim Graham Photo Library via Getty Images

While dropping her sons off at school in 1989, Princess Diana threw on a checkered blazer over a sweatshirt and a pair of sweatpants.

She finished off the casual look with brown embellished boots and a navy baseball cap.

Her casual looks were just as stylish as her lavish gowns, including this pink bee sweater.

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Princess Diana and Prince William on the Scilly Isles in 1989.AP

The whole family was dressed for a spin around the island of Tresco in the summer of 1989.

Princess Diana wore a bright-pink sweater with bee embellishments and finished off the look with simple, white pants.

She could combine contrasting colors in the perfect way.

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Princess Diana wore this Catherine Walker look during a visit to Hong Kong.Princess Diana Archive / Stringer/ Getty

Princess Diana's colorful style is showcased in this polished red and purple look.

She wore this chic Catherine Walker ensemble during a visit to Hong Kong in 1989.

She knew how to work her Sunday best.

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Princess Diana with Prince William in 1990.Tim Graham / Contributor/Getty

While leaving a church service with Prince William in 1990, the princess donned this striking outfit that featured a houndstooth print.

The princess nailed the casual "1990s mom" look on several occasions.

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Princess Diana wearing a Philadelphia Eagles letterman jacket.AP

While dropping her sons off at school in 1981, the princess wore an oversized NFL Philadelphia Eagles letterman jacket over a simple black skirt and shirt.

She wore another bold, one-shoulder look on an official trip to Brazil.

Princess Diana Brazil 1991
Princess Diana in a floral Catherine Walker gown during a 1991 trip to Brazil.Tim Graham Photo Library.

When Princess Diana traveled to Brazil in 1991 for an official visit, she wore another daring neckline.

This pink and white floral gown was designed by Catherine Walker.

On another skiing trip, Princess Diana rocked an all-denim jumpsuit after hitting the slopes.

princess diana denim jumpsuit 1993
Princess Diana with her sons Prince William and Prince Harry on holiday in 1993.Tim Graham Photo Library via Getty Images

The princess rocked a classic 1990s denim look while on a skiing trip with her two sons in 1993.

The denim jumpsuit was layered under an oversized bomber-style jacket and paired with bright-white boots.

On a trip to Disney World, the princess once again showed off her casual style.

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Princess Diana with her sons on a trip to Disney World in Orlando, Florida.Chris O’Meara/AP

On a 1993 trip to Disney World in Orlando, Florida, Princess Diana rocked a classic 1990s mom look in high-waisted khaki shorts and a tucked white T-shirt.

Many have called this her "Revenge Dress."

princess diana revenge dress
No other royal had dared to wear this style of dress before.Jayne Fincher/Getty Images

In 1994, on the night that the controversial Prince Charles documentary aired (in which he admitted to having an affair), the princess arrived at the Serpentine Gallery wearing a black dress with a plunging neckline.

This velvet, off-the-shoulder minidress was a look that no other royal before her had dared to wear.

To this day, the frock has been widely dubbed "The Revenge Dress."

Princess Diana seemingly channeled an American icon with this look.

princess diana outfits
Princess Diana resembled Jackie Kennedy's iconic look.Jayne Fincher/Getty Images

Princess Diana seemingly channeled Jackie Kennedy's famed pink outfit in this Versace skirt suit during this 1995 outing to the Howe Barracks in Canterbury, Kent.

She could rock any kind of neckline.

princess diana neckline
Princess Diana wore this look to the Serpentine Gallery.Princess Diana Archive / Stringer

This beaded dress with a shocking, plunging neckline was perfect for Princess Diana's summertime appearance at the Serpentine Gallery in 1995.

And who can forget one of Princess Diana's most famous casual looks?

princess diana t shirt shorts
The Virgin-Atlantic sweatshirt would later be auctioned off.Anwar Hussein/WireImage/Getty

In 1995, the princess showed off this casual look that featured bright-orange bike shorts, sneakers, and a Virgin-Atlantic sweatshirt.

Years later, in July 2019, the sweatshirt was auctioned off. According to Vanity Fair, it sold for $53,532.

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